CA2683059C - Atropisomer of pyrrole derivative - Google Patents
Atropisomer of pyrrole derivative Download PDFInfo
- Publication number
- CA2683059C CA2683059C CA2683059A CA2683059A CA2683059C CA 2683059 C CA2683059 C CA 2683059C CA 2683059 A CA2683059 A CA 2683059A CA 2683059 A CA2683059 A CA 2683059A CA 2683059 C CA2683059 C CA 2683059C
- Authority
- CA
- Canada
- Prior art keywords
- phenyl
- atropisomer
- pyrrole
- group
- trifluoromethyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- 150000003233 pyrroles Chemical class 0.000 title description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 56
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- 229940124597 therapeutic agent Drugs 0.000 claims abstract description 12
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 7
- 208000024172 Cardiovascular disease Diseases 0.000 claims abstract description 5
- 206010020772 Hypertension Diseases 0.000 claims description 12
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 7
- NOSNHVJANRODGR-UHFFFAOYSA-N 1-(2-hydroxyethyl)-4-methyl-n-(4-methylsulfonylphenyl)-5-[2-(trifluoromethyl)phenyl]pyrrole-3-carboxamide Chemical compound CC=1C(C(=O)NC=2C=CC(=CC=2)S(C)(=O)=O)=CN(CCO)C=1C1=CC=CC=C1C(F)(F)F NOSNHVJANRODGR-UHFFFAOYSA-N 0.000 claims description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- GZYITUOKAFASGJ-UHFFFAOYSA-N 1,4-dimethyl-n-(4-methylsulfonylphenyl)-5-[2-(trifluoromethyl)phenyl]pyrrole-3-carboxamide Chemical compound CC=1C(C(=O)NC=2C=CC(=CC=2)S(C)(=O)=O)=CN(C)C=1C1=CC=CC=C1C(F)(F)F GZYITUOKAFASGJ-UHFFFAOYSA-N 0.000 claims description 5
- GUFSSXYHGZUYDC-UHFFFAOYSA-N 1-(2-hydroxyethyl)-5-[4-methoxy-2-(trifluoromethyl)phenyl]-4-methyl-n-(4-methylsulfonylphenyl)pyrrole-3-carboxamide Chemical compound FC(F)(F)C1=CC(OC)=CC=C1C1=C(C)C(C(=O)NC=2C=CC(=CC=2)S(C)(=O)=O)=CN1CCO GUFSSXYHGZUYDC-UHFFFAOYSA-N 0.000 claims description 5
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- 125000006273 (C1-C3) alkyl group Chemical group 0.000 abstract description 4
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- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
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- PQSUYGKTWSAVDQ-UHFFFAOYSA-N Aldosterone Natural products C1CC2C3CCC(C(=O)CO)C3(C=O)CC(O)C2C2(C)C1=CC(=O)CC2 PQSUYGKTWSAVDQ-UHFFFAOYSA-N 0.000 description 2
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- 230000004568 DNA-binding Effects 0.000 description 2
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
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- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
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- WNIGQHYWJMGCDU-UHFFFAOYSA-N methyl 4-methyl-5-[2-(trifluoromethyl)phenyl]-1h-pyrrole-3-carboxylate Chemical compound COC(=O)C1=CNC(C=2C(=CC=CC=2)C(F)(F)F)=C1C WNIGQHYWJMGCDU-UHFFFAOYSA-N 0.000 description 2
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- HBZBAMXERPYTFS-SECBINFHSA-N (4S)-2-(6,7-dihydro-5H-pyrrolo[3,2-f][1,3]benzothiazol-2-yl)-4,5-dihydro-1,3-thiazole-4-carboxylic acid Chemical compound OC(=O)[C@H]1CSC(=N1)c1nc2cc3CCNc3cc2s1 HBZBAMXERPYTFS-SECBINFHSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
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- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
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- 238000007259 addition reaction Methods 0.000 description 1
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- KYITYFHKDODNCQ-UHFFFAOYSA-M sodium;2-oxo-3-(3-oxo-1-phenylbutyl)chromen-4-olate Chemical compound [Na+].[O-]C=1C2=CC=CC=C2OC(=O)C=1C(CC(=O)C)C1=CC=CC=C1 KYITYFHKDODNCQ-UHFFFAOYSA-M 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A61P9/00—Drugs for disorders of the cardiovascular system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
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- A—HUMAN NECESSITIES
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- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P9/12—Antihypertensives
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| JP2007-101938 | 2007-04-09 | ||
| JP2007101938 | 2007-04-09 | ||
| PCT/JP2008/056907 WO2008126831A1 (ja) | 2007-04-09 | 2008-04-08 | ピロール誘導体のアトロプ異性体 |
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| CA2683059A1 CA2683059A1 (en) | 2008-10-23 |
| CA2683059C true CA2683059C (en) | 2012-09-25 |
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| WO2010042622A1 (en) * | 2008-10-08 | 2010-04-15 | Exelixis, Inc. | Atropisomers of (hydroxyalkyl) pyrrole derivatives |
| AU2009302375B2 (en) | 2008-10-08 | 2015-03-26 | Exelixis, Inc. | 1-phenylpyrrole compounds |
| WO2010098286A1 (ja) * | 2009-02-25 | 2010-09-02 | 第一三共株式会社 | ミネラルコルチコイド受容体拮抗薬を含有する医薬 |
| EP2411375B1 (en) * | 2009-03-26 | 2013-08-28 | Poxel | Process for enantiomeric separation of racemic dihydro-1,3,5 triazines via preferential crystallization |
| CA2908879C (en) | 2013-04-10 | 2018-05-15 | Daiichi Sankyo Company, Limited | Crystal of pyrrole derivative and method for producing the same |
| ES2847904T3 (es) * | 2013-07-23 | 2021-08-04 | Daiichi Sankyo Co Ltd | Medicamento para la prevención o el tratamiento de la hipertensión |
| EP3040330B1 (en) * | 2013-08-27 | 2018-01-10 | Daiichi Sankyo Company, Limited | Method for producing pyrrole derivative, and intermediate thereof |
| RS58274B1 (sr) | 2014-06-30 | 2019-03-29 | Astrazeneca Ab | Benzoksazinon amidi kao modulatori mineralokortikoidnog receptora |
| KR102488167B1 (ko) * | 2015-01-26 | 2023-01-12 | 다이이찌 산쿄 가부시키가이샤 | 피롤카르복사미드의 고형 조성물 |
| CN109053608A (zh) * | 2015-02-17 | 2018-12-21 | 华润赛科药业有限责任公司 | 一种旋光纯的硫代乙酸类化合物、其药物组合物和用途 |
| CN105622531A (zh) | 2015-04-03 | 2016-06-01 | 南京明德新药研发股份有限公司 | 轴手性异构体及其制备方法和制药用途 |
| JP6835836B2 (ja) | 2015-10-13 | 2021-02-24 | アンスティチュ ナショナル ドゥ ラ サンテ エ ドゥ ラ ルシェルシュ メディカル | 脈絡膜血管新生の処置のための方法及び医薬組成物 |
| EP3434284A4 (en) * | 2016-03-24 | 2019-11-13 | Daiichi Sankyo Company, Limited | MEDICINE FOR THE TREATMENT OF KIDNEY DISEASE |
| US20190262363A1 (en) | 2016-07-26 | 2019-08-29 | INSERM (Institut National de la Santé et de la Recherche Médicale | Antagonist of mineralocorticoid receptor for the treatment of osteoarthritis |
| AU2020371836A1 (en) | 2019-10-25 | 2021-11-11 | Sunshine Lake Pharma Co., Ltd. | Pyrrole amide compound and use thereof |
| EP4118235A1 (en) | 2020-03-11 | 2023-01-18 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Methods of determining whether a subject has or is at risk of having a central serous chorioretinopathy |
| AU2022248168A1 (en) * | 2021-03-30 | 2023-10-05 | Sunshine Lake Pharma Co., Ltd. | Crystalline form of pyrrole amide compound, preparation method therefor and use thereof |
| AU2022264993A1 (en) * | 2021-04-26 | 2023-11-09 | Sunshine Lake Pharma Co., Ltd. | Preparation method for pyrrole amide compound |
| WO2023031277A1 (en) | 2021-08-31 | 2023-03-09 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Methods for the treatment of ocular rosacea |
| CN115784961A (zh) * | 2021-09-10 | 2023-03-14 | 上海鼎雅药物化学科技有限公司 | 埃沙西林酮及其中间体的合成方法 |
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| US6323208B1 (en) | 1997-09-05 | 2001-11-27 | Pfizer Inc | Atropisomers of 2,3-disubstituted-(5.6)-heteroaryl fused-pyrimidin-4-ones |
| US20040267028A1 (en) * | 2001-09-24 | 2004-12-30 | Smith Roger A | Preparation and use of pyrrole derivatives for treating obesity |
| US6939968B2 (en) | 2002-12-23 | 2005-09-06 | Bristol-Myers Squibb Company | Atropisomers of 3-substituted-4-arylquinolin-2-one derivatives |
| DE10354060A1 (de) * | 2003-11-19 | 2005-06-02 | Merck Patent Gmbh | Pyrrolderivate |
| HUE041596T2 (hu) * | 2004-07-30 | 2019-05-28 | Exelixis Inc | Pirrol származékok mint gyógyászati szerek |
| CA2593156C (en) * | 2005-01-10 | 2015-05-05 | Exelixis, Inc. | Heterocyclic carboxamide compounds as steroid nuclear receptors ligands |
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Also Published As
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| CN101679243B (zh) | 2012-09-26 |
| JPWO2008126831A1 (ja) | 2010-07-22 |
| US20100093826A1 (en) | 2010-04-15 |
| KR101477579B1 (ko) | 2014-12-30 |
| US8524918B2 (en) | 2013-09-03 |
| TW200901968A (en) | 2009-01-16 |
| EP2133330A4 (en) | 2010-08-11 |
| JP5363312B2 (ja) | 2013-12-11 |
| ES2448498T3 (es) | 2014-03-14 |
| TWI444185B (zh) | 2014-07-11 |
| PT2133330E (pt) | 2014-03-31 |
| BRPI0809656B8 (pt) | 2021-05-25 |
| IL201261A0 (en) | 2010-05-31 |
| BRPI0809656A2 (pt) | 2014-10-07 |
| KR20090127421A (ko) | 2009-12-11 |
| EP2133330B1 (en) | 2014-01-01 |
| PL2133330T3 (pl) | 2014-06-30 |
| CN101679243A (zh) | 2010-03-24 |
| HK1139942A1 (en) | 2010-09-30 |
| US20140024696A1 (en) | 2014-01-23 |
| BRPI0809656B1 (pt) | 2019-07-09 |
| WO2008126831A1 (ja) | 2008-10-23 |
| US8754118B2 (en) | 2014-06-17 |
| DK2133330T3 (da) | 2014-03-31 |
| CA2683059A1 (en) | 2008-10-23 |
| EP2133330A1 (en) | 2009-12-16 |
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